Sales Development Representative

About Feathery

Feathery is a platform that helps organizations automate data intake processes through advanced form and document AI. Teams use it to run everything from client onboarding to insurance underwriting and other workflow-heavy operations.

The product gives business users a single system for creating data-focused user journeys end to end. As adoption grows, the company is expanding its go-to-market team to reach more complex and larger enterprise customers.

Why This Role Exists

Feathery is growing quickly and working with an increasing number of organizations that want to modernize their workflows. The company is looking for a Sales Development Representative to build pipeline, support demand creation, and help establish the core sales motion.

This position is a strong fit for someone who enjoys fast-moving environments, likes building processes from scratch, and wants to contribute to a high-growth B2B SaaS business at an early stage of team growth.

As one of the early hires in this function, you will help shape how the company approaches outbound, demand generation, and customer engagement.

Role Overview

This is a broad ownership role that combines outbound prospecting, inbound lead qualification, experimentation with outreach approaches, and collaboration across go-to-market teams.

You will support the growth of the revenue engine by developing outreach strategies, engaging prospective customers, and helping refine how the company presents itself in the market.

Key Responsibilities

• Find and reach out to new accounts by explaining how Feathery can improve and automate their workflows.
• Contact prospects through email, LinkedIn, and phone outreach.
• Test different audiences, messages, and channels to create enterprise opportunities.
• Own pipeline generation efforts and keep improving results over time.
• Handle inbound interest from potential customers.
• Assess leads for fit and decide which opportunities should be prioritized.
• Run discovery calls to learn about customer needs, pain points, and objectives.
• Keep organized notes and observations on prospect conversations.
• Meet prospects in Zoom calls and in person when needed.
• Learn the product thoroughly and create demos tailored to different buyer types.
• Present Feathery’s value in a clear, persuasive, and customer-focused way.
• Help improve outbound playbooks and sales workflows.
• Work with marketing, product, and leadership on go-to-market efforts.
• Share customer feedback to support product decisions and market positioning.
• Assist with product launches and other initiatives that need customer-facing support.

What We’re Looking For

• Excellent communication skills and the ability to quickly build rapport and trust.
• Strong empathy and the ability to adjust messaging for different audiences.
• A history of strong performance in academics, work, or extracurricular activities.
• A builder mentality and interest in creating and improving systems from the ground up.
• Self-driven, resilient, and comfortable working through uncertainty.
• Genuine interest in understanding customer problems and helping solve them.
• Enjoyment of networking, relationship-building, and meeting new people.
• Enthusiasm for joining a fast-growing startup and contributing to revenue growth.

Bonus Experience

• Previous exposure to outbound prospecting or cold outreach through calls, email, or LinkedIn.
• Experience in a B2B SaaS sales or go-to-market role.
• Familiarity with CRM systems and outbound sales tools.
• Background in financial services or other workflow-intensive industries.

Benefits and Workplace

• Competitive pay plus equity participation.
• Health, dental, and vision insurance coverage.
• Unlimited paid time off.
• Office located in downtown Toronto.
• Snacks in the office and a catered lunch every month.
• A collaborative, low-ego culture that values ownership and professional growth.
• Company offsite for team connection and relaxation.

Equal Opportunity

Feathery is an equal opportunity employer. Hiring decisions are made without regard to race, religion, color, national origin, sex, sexual orientation, age, veteran status, disability, genetic information, or any other protected characteristic. Reasonable accommodations are available upon request.